The first baseball game I ever saw live was a Cubs-Brewers game at six years old. Yet, the first sports team apparel I ever wore was a toddler-sized Indians’ jersey.

I have lived in the Chicago suburbs my entire life, and I have taken the city’s teams as my own. However, because I was born to two parents born and raised just outside of Cleveland, I’ve always reserved a soft spot in my heart for Cleveland sports. Unless the team was playing the Cubs, I’ve always rooted for the Indians as my second team. Due to both teams’ history, I never thought I’d have to take sides in a World Series.

Well, I was wrong. At the beginning of the MLB playoffs this year, my dad semi-seriously texted me “Looking forward to a Cubs-Indians World Series this year!” I was excited and conflicted by the idea, but I was sure it wouldn’t happen. At the very least, one of the teams would find a way to exit the playoffs early.

Three weeks later, the impossible happened. Both teams I grew up rooting for are playing for the title of World Series Champion.

Though I’m conflicted, this is by far the most fun I’ve had watching a World Series in my life. I went home to watch Game 1 and 2 with my dad. It was great to watch each team win, and even when I was upset when the Cubs fell 6-0 in the first game, it was worth it to see my dad’s reaction when the Indians won.

I’ve also had a lot of fun by messing with my extended family, most of who still live in Cleveland. Before the series began Tuesday, my cousin and I heckled each other all day in a series of Snapchat videos where he tried to get me to wear my Kluber shirt.

Aside from my personal connection, the teams share a troubled past with one another and have struggled for success.

In the 2003 National League Championship Series (NLCS), the Cubs played the then Florida Marlins and went up three games to one in five with the final two games to be played at Wrigley Field. With five outs needed to win Game 6, Cubs fan Steve Bartman reached out for a foul ball, preventing outfielder Moisés Alou from catching the ball cleanly. The Cubs ended up letting the Marlins score eight runs in the inning and the Marlins won the game and, ultimately, the Series.

Likewise, in the 2007 American League Championship Series (ALCS), the Indians played the Boston Red Sox, and were also up three games to one. Boston ended up taking the Series to Game 7 and winning.

The teams hold the number one and two spots of the longest World Series Champion droughts. The Cubs last won in 1908 and the Indians won their last in 1948. Both streaks are currently ongoing, one of which will conclude this season.

My dad, unsurprisingly, is the biggest Indians fan I know. Like myself, he has had to sit through the ups and, specifically, downs of his team. He was born in 1954, the same year the Indians ended the regular season with 111-43 which, at the time, was the American League’s best regular season record. The Indians concluded that year by being swept in the World Series by the then New York Giants.

The Indians didn’t see much success until the 1990s when the team had two World Series appearances in 1995 and 1997, but lost both.

The Cubs haven’t had as much success. Before this Series, the Cubs had never made it past the NLCS and have struggled before and during my lifetime. In 2012 it was especially hard to watch the Cubs. A year after signing ex-Boston Red Sox general manager Theo Epstein as president of Baseball Operations, the Cubs ended their 2012 season with a 61-101 record. The hardships, no matter how hard, have made the success all the more sweeter for each team.

Although this World Series has made me root against the team of my forefathers, it is the most fun I’ve had watching baseball in years. In the end, I still have to say…

“Go Cubs.”